Japanese Unexamined Patent Application, First Publication No. Hei 11-269176 (WO99/29689, EP-A-1038874) and Japanese Unexamined Patent Application, First Publication No. 2001-55387 (WO00/75138, EP-A-1184382) according to an invention of the present inventors disclose that hetero ring-substituted oxime derivatives act as plant disease controlling agents.
Specifically, Japanese Unexamined Patent Application, First Publication No. Hei 11-269176 (WO99/29689, EP-A-1038874) discloses oxime derivatives represented by the general formula (A):
wherein R1 represents a hydrogen atom or a lower alkyl group; X represents a halogen atom, a nitro group, a hydroxy group, a cyano group, a carboxyl group, an alkoxycarbonyl group, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, an aryl group, an aryloxy group, or an amino group; n represents an integer of 0 to 3; Het A represents a six-membered nitrogen-containing aromatic ring having one or more nitrogen atoms, which may be substituted with one or more substituents selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkoxy group, a trifluoromethyl group and a cyano group, or a benzo condensed ring type nitrogen-containing aromatic ring; and Het B represents a group represented by an one of the ring structures of the general formula:
the general formula:
and the general formula:
(wherein Y represents a hydrogen atom, a halogen atom, or a lower alkyl group).
Also Japanese Unexamined Patent Application, First Publication No.2001-55387 (WO00/75138, EP-A-1184382) discloses oxime derivatives represented by the general formula (B):
wherein Het A represents a group represented by any one of the following three formulas:
(wherein Q represents a hydrogen atom, a halogen atom, or a lower alkyl group; R1 represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, an aralkyl group, or an aryl group; and R2 represents a hydrogen atom or a lower alkyl group); Het B represents a group represented by any one of the following nine formulas:
(wherein Y represents a hydrogen atom or a lower alkyl group; and R3 represents a hydrogen atom or a lower alkyl group); and Het C represents a group represented by any one of the following nine formulas:
(wherein R4 represents a hydrogen atom or a lower alkyl group; X represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, or a cyano group; Z represents a hydrogen atom, a halogen atom, or a lower alkyl group, and n represents an integer of 0 to 3).
Although the respective compounds described in Japanese Unexamined Patent Application, First Publication No. Hei 11-269176 (WO99/29689, EP-A-1038874) and Japanese Unexamined Patent Application, First Publication No. 2001-55387 (WO00/75138, EP-A-1184382) exhibit considerable control activity, it is particularly necessary to develop chemicals which exert superior control activity.
The document (Bull. Soc. Chim. Belg., Vol. 96, page 675, 1987) discloses only compounds similar to tetrazoylhydroxime derivatives represented by the general formula (7) described in claim 9 of the present invention, which are suited for use as an intermediate for synthesis of tetrazoyloxime derivatives described in claim 1 of the present invention, for example, compound of the general formula (7) X2 is a hydrogen atom and Y2 is a methyl group, compound wherein X2 is a hydrogen atom and Y2 is an isopropyl group, and compound wherein X2 is a chlorine atom and Y2 is a methyl group. These three compounds were synthesized during research for the purpose of elucidation of a reaction mechanism. The document does not disclose the utility of these compounds, for example, tetrazoyloxime derivatives represented by the general formula (1) described in claim 1 of the present invention can be synthesized by using the compounds and the compounds are suited for use as an intermediate for preparation of an agricultural chemical.